Dioxolane substituted anilids

ABSTRACT

This invention discloses new compounds of the formula ##SPC1## 
     Wherein Y is selected from the group consisting of hydrogen, lower alkyl and halogen; R 1  is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy; R 2  is lower alkyl; R 3  and R 4  are independently selected from the group consisting of hydrogen and lower alkyl; X is halogen; and n is the integer 1 or 2. The compounds of the above description are useful as herbicides.

This invention relates to new compositions of matter and morespecifically relates to new compounds of the formula ##SPC2##

Wherein Y is selected from the group consisting of hydrogen, lower alkyland halogen; R¹ is selected from the group consisting of hydrogen, loweralkyl and lower alkoxy; R² is lower alkyl; R³ and R⁴ are independentlyselected from the group consisting of hydrogen and lower alkyl; X ishalogen; and n is the integer 1 or 2.

The term lower as used herein designates a straight or branched carbonchain of up to and including 6 carbon atoms.

The compounds of the present invention are unexpectedly useful asherbicides and are particularly useful in controlling grassy weeds.

In a preferred embodiment of the present invention Y is hydrogen and Xis chlorine or bromine.

The compounds of the present invention can be prepared by reacting acompound of the formula ##SPC3##

Wherein Y, R¹, R², R⁴ and n are as heretofore described, with anα-haloalkanoyl chloride of the formula

    O                                                                             ∥                                                                    Cl--C--CHX                                                                    |                                                                    s,67 R.sup.3                                                                              (III)                                                         

wherein R³ and X are as heretofore described. This reaction can beeffected by combining a compound of formula II with a compound offormula III in an inert organic reaction medium, such as dioxane orbenzene, in the presence of an acid acceptor, such as an alkali metalcarbonate or bicarbonate, at a temperature of from about -10°C to about25°C and stirring the resulting mixture for a period of from about 15 toabout 120 minutes. The reaction mixture can then be heated attemperatures ranging up to the reflux temperature of the reactionmixture to ensure completion of the reaction. After this time thereaction mixture can be washed with water to remove inorganic salts andstripped of solvent to yield the desired product. This product can beused as such or can be further purified by conventional techniques.

The compounds of formula II can be prepared by reacting a substitutedaniline of the formula ##SPC4##

Wherein Y, R¹ and R² are as heretofore described, with a compound of theformula ##EQU1## wherein R⁴ and n are as heretofore described. Thisreaction can be effected by combining a compound of formula IV with acompound of formula V in an inert organic reaction medium if desired inthe presence of an acid acceptor such as an alkali metal carbonate andheating the resulting mixture at reflux for a period of from about 1 toabout 48 hours. After this time the mixture can be filtered anddistilled to yield the desired product.

The compounds of formula V when not readily available can be prepared byreacting a glycol of the formula ##EQU2## wherein n is as heretoforedescribed, with an aldehyde of the formula

    R.sup.4 CHO                                                (VII)

wherein R⁴ is as heretofore described. This reaction can be effected bycombining the compounds of formulae VI and VII in an inert reactionmedium such as benzene and in the presence of a catalyst such as calciumchloride or toluenesulfonic acid. The reaction mixture can then beheated at reflux until no more water can be removed by azeotropicdistillation. After this time the reaction mixture can be filtered anddistilled under vacuum to yield the desired product.

Exemplary aldehydes of formula VII are formaldehyde, propionaldehyde,butyraldehyde, pentanal, hexanal, heptanal and the like.

Exemplary substituted anilines of formula IV useful in preparing thecompounds of formula II are 2-methylaniline, 2-ethylaniline,2-propylaniline, 2-isopropylaniline, 2-butylaniline, 2-hexylaniline,2,6-dimethylaniline, 2,6-diethylaniline, 2,6-dipropylaniline,2,6-dibutylaniline, 2,6-dihexylaniline, 2-methoxy-6-methylaniline,2-methoxy-6-ethylaniline, 2-ethoxy-6-methylaniline,2-ethoxy-6-ethylaniline, 2-propoxy-6-methylaniline,2-butoxy-6-ethylaniline, 2-hexyloxy-6-methylaniline,2,4,6-trimethylaniline, 2,4,6-triethylaniline, 2,4,6-tripropylaniline,2,6-dimethyl-4-butylaniline, 2,4-dimethylaniline, 2,4-diethylaniline,2-methyl-4-chloroaniline, 2-methyl-3-bromoaniline,2-methyl-4-iodoaniline, 2-methyl-4-fluoroaniline and the like.

Exemplary α-haloalkanoyl chlorides of formula III are chloroacetylchloride, bromoacetyl chloride, iodoacetyl chloride, α-chloropropanoylchloride, α-bromopropanoyl chloride, α-chlorobutanoyl chloride,α-chloropentanoyl chloride, α-chlorohexanoyl chloride, α-bromooctanoylchloride and the like.

The preparation of the compounds of the present invention is morespecifically illustrated in the following examples.

EXAMPLE 1 Preparation of 5-Chloromethyl-1,3-dioxolane

3-Chloropropandiol-1,2 (60 grams), paraformaldehyde (25 grams),toluenesulfonic acid (0.5 grams) and benzene (200 ml) were charged intoa glass reaction vessel equipped with a mechanical stirrer, thermometerand reflux condenser with a Dean-Stark trap. The reaction mixture washeated at reflux until no more water was removed by azeotropicdistillation. After this time the reaction mixture was stripped ofbenzene and distilled to yield the desired product5-chloromethyl-1,3-dioxolane as an oil having a boiling point of 47°Cunder aspirator pressure.

EXAMPLE 2 Preparation of N-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethylaniline

2,6-Dimethylaniline (94.5 grams), 5-chloromethyl-1,3-dioxolane (31.8grams), potassium carbonate (36.7 grams) and tetraethylammonium chloride(2 grams) were charged into a glass reaction vessel equipped with amechanical stirrer, thermometer and reflux condenser. The reactionmixture was heated at reflux for a period of 48 hours. After this timethe mixture was filtered and distilled to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2,6-dimethylaniline having a boiling pointof 132°C under aspirator pressure.

EXAMPLE 3 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethyl-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethylaniline (22.4 grams), sodiumcarbonate (11.5 grams), water (100 ml) and benzene (100 ml) were chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The mixture was cooled to a temperature of about 0°C andchloroacetyl chloride (8.2 ml) was slowly added with stirring. After theaddition was completed stirring was continued for a period of about onehour. The mixture was then washed with water, was dried and distilled toyield the desired productN-(1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-α-chloroacetanilide as an oilboiling at 200°-205°C at 1 mm of Hg pressure.

EXAMPLE 4 Preparation of 5-β-Chloroethyl-1,3-dioxolane

4-Chlorobutandiol-1,2 (0.5 mole), paraformaldehyde (0.55 mole),toluenesulfonic acid (1 gram) and benzene (250 ml) are charged into aglass reaction vessel equipped with a mechanical stirrer, thermometerand reflux condenser with a Dean-Stark trap. The reaction mixture isheated at reflux until no more water is removed by azeotropicdistillation. After this time the reaction mixture is stripped ofsolvent and is distilled to yield the desired product5-β-chloroethyl-1,3-dioxolane.

EXAMPLE 5 Preparation of N-(1,3-Dioxolan-5-ylethyl)-2,6-diethylaniline

2,6-Diethylaniline (0.3 mole, 5-β-chloroethyl-1,3-dioxolane (0.3 mole),potassium carbonate (0.3 mole) and tetraethylammonium chloride (2 grams)are charged into a glass reaction vessel equipped with a mechanicalstirrer, thermometer and reflux condenser. The reaction mixture isheated at reflux for a period of 4 hours. After this time the mixture isfiltered to yield the desired productN-(1,3-dioxolan-5-ylethyl)-2,6-diethylaniline.

EXAMPLE 6 Preparation ofN-(1,3-Dioxolan-5-ylethyl)-2,6-diethyl-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylethyl)-2,6-diethylaniline (0.1 mole), sodiumcarbonate (0.1 mole), water (10 ml) and benzene (100 ml) are chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The reaction mixture is cooled to a temperature of about0°C and chloroacetyl chloride (0.11 mole) is incrementally added withstirring. After the addition is completed, stirring is continued for aperiod of about one hour. The mixture is then washed with water, driedover anhydrous magnesium sulfate and filtered. The filtrate is strippedof solvent and unreacted starting materials to yield the desired productN-(1,3-dioxolan-5-ylethyl)-2,6-diethyl-α-chloroacetanilide as theresidue.

EXAMPLE 7 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2-methyl-6-methoxyaniline

2-Methyl-6-methoxyaniline (0.3 mole), 5-chloromethyl-1,3-dioxolane (0.3mole), potassium carbonate (0.3 mole) and tetraethylammonium chloride (2grams) are charged into a glass reaction vessel equipped with amechanical stirrer, thermometer and reflux condenser. The reactionmixture is heated at reflux for a period of 4 hours. After this time themixture is filtered and distilled to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-methoxyaniline.

EXAMPLE 8 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2-methyl-6-methoxy-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylmethyl)-2-methyl-6-methoxyaniline (0.1 mole), sodiumcarbonate (0.1 mole), water (10 ml) and benzene (100 ml) are chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The reaction mixture is cooled to a temperature of about0°C and chloroacetyl chloride (0.11 mole) is incrementally added withstirring. After the addition is completed, stirring is continued for aperiod of about one hour. The mixture is then washed with water, driedover anhydrous magnesium sulfate and filtered. The filtrate is strippedof solvent and unreacted starting materials to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-methoxy-α-chloroacetanilide asthe residue.

EXAMPLE 9 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2-ethyl-4-chloroaniline

2-Ethyl-4-chloroaniline (0.3 mole), 5-chloromethyl-1,3-dioxolane (0.3mole), potassium carbonate (0.3 mole) and tetraethylammonium chloride (2grams) are charged into a glass reaction vessel equipped with amechanical stirrer, thermometer and reflux condenser. The reactionmixture is heated at reflux for a period of 6 hours. After this time themixture is filtered and distilled to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2-ethyl-4-chloroaniline.

EXAMPLE 10 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2-ethyl-4-chloro-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylmethyl)-2-ethyl-4-chloroaniline (0.1 mole), sodiumcarbonate (0.1 mole), water (10 ml) and benzene (100 ml) are chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The reaction mixture is cooled to a temperature of about0°C and chloroacetyl chloride (0.11 mole) is incrementally added withstirring. After the addition is completed, stirring is continued for aperiod of about one hour. The mixture is then washed with water, driedover anhydrous magnesium sulfate and filtered. The filtrate is strippedof solvent and unreacted starting materials to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2-ethyl-4-chloro-α-chloroacetanilide as theresidue.

EXAMPLE 11 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2,4,6-trimethylaniline

2,4,6-Trimethylaniline (0.3 mole), 5-chloromethyl-1,3-dioxolane (0.3mole), potassium carbonate (0.3 mole) and tetraethylammonium chloride (2grams) are charged into a glass reaction vessel equipped with amechanical stirrer, thermometer and reflux condenser. The reactionmixture is heated at reflux for a period of 8 hours. After this time themixture is filtered and distilled to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2,4,6-trimethylaniline.

EXAMPLE 12 Preparation ofN-(1,3-Dioxolan-5-ylmethyl-2,4,6-trimethyl-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylmethyl)-2,4,6-trimethylaniline (0.1 mole), sodiumcarbonate (0.1 mole), water (10 ml) and benzene (100 ml) are chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The reaction mixture is cooled to a temperature of about0°C and chloroacetyl chloride (0.11 mole) is incrementally added withstirring. After the addition is completed, stirring is continued for aperiod of about one hour. The mixture is then washed with water, driedover anhydrous magnesium sulfate and filtered. The filtrate is strippedof solvent and unreacted starting materials to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2,4,6-trimethyl-α-chloroacetanilide as theresidue.

EXAMPLE 13 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromoaniline

2,6-Dimethyl-4-bromoaniline (0.3 mole), 5-chloromethyl-1,3-dioxolane(0.3 mole), potassium carbonate (0.3 mole) and tetraethylammoniumchloride (2 grams) are charged into a glass reaction vessel equippedwith a mechanical stirrer, thermometer and reflux condenser. Thereaction mixture is heated at reflux for a period of 5 hours. After thistime the mixture is filtered and distilled to yield the desired productN-(1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromoaniline.

EXAMPLE 14 Preparation ofN-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromo-α-chloroacetanilide

N-(1,3-Dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromoaniline (0.1 mole),sodium carbonate (0.1 mole), water (10 ml) and benzene (100 ml) arecharged into a glass reaction vessel equipped with a mechanical stirrerand thermometer. The reaction mixture is cooled to a temperature ofabout 0°C and chloroacetyl chloride (0.11 mole) is incrementally addedwith stirring. After the addition is completed, stirring is continuedfor a period of about one hour. The mixture is then washed with water,dried over anhydrous magnesium sulfate and filtered. The filtrate isstripped of solvent and unreacted starting materials to yield thedesired productN-(1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromo-α-chloroacetanilide asthe residue.

EXAMPLE 15 Preparation of 2-Methyl-5-chloromethyl-1,3-dioxolane

3-Chloropropandiol-1,2 (0.5 mole), acetaldehyde (0.5 mole),toluenesulfonic acid (0.5 grams) and benzene (200 ml) are charged into aglass reaction flask equipped with a mechanical stirrer, thermometer andreflux condenser with a Dean-Stark trap. The reaction mixture is heatedat reflux until no more water is removed by azeotropic distillation.After this time the reaction mixture is stripped of solvent and isdistilled to yield the desired product2-methyl-5-chloromethyl-1,3-dioxolane.

EXAMPLE 16 Preparation ofN-(2-Methyl-1,3-dioxolan-5-ylmethyl)-2-t-butylaniline

2-t-Butylaniline (0.3 mole), 2-methyl-5-chloromethyl-1,3-dioxolane (0.3mole), potassium carbonate (0.3 mole) and tetraethylammonium chloride (2grams) are charged into a glass reaction vessel equipped with amechanical stirrer, thermometer and reflux condenser. The reactionmixture is heated at reflux for a period of 48 hours. After this timethe mixture is filtered to yield the desired productN-2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butylaniline.

EXAMPLE 17 Preparation ofN-(2-Methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-α-bromoacetanilide

N-(2-Methyl-1,3-dioxolan-5-ylmethyl)-2-t-butylaniline (0.1 mole), sodiumcarbonate (0.1 mole), water (10 ml) and benzene (100 ml) are chargedinto a glass reaction vessel equipped with a mechanical stirrer andthermometer. The reaction mixture is cooled to a temperature of about0°C and bromoacetyl chloride (0.11 mole) is incrementally added withstirring. After the addition is completed, stirring is continued for aperiod of about one hour. The mixture is then washed with water, driedover anhydrous magnesium sulfate and filtered. The filtrate is strippedof solvent and unreacted starting materials to yield the desired productN-(2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-α-bromoacetanilide as theresidue.

Additional exemplary compounds which can be prepared according to theprocedures of the foregoing examples areN-(2-ethyl-1,3-dioxolan-5-ylmethyl)-2,6-dipropyl-α-iodoacetanilide,N-(2-propyl-1,3-dioxolan-5-ylmethyl)-2,6-dibutyl-α-fluoroacetanilide,N-(2-butyl-1,3-dioxolan-5-ylmethyl)-2,6-dihexyl-α-chloroacetanilide,N-(2-hexyl-1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-ethoxy-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-propoxy-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-butoxy-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-pentyloxy-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-hexyloxy-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2,4-diethyl-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-methyl-4-propyl-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-methoxy-4-butyl-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-methoxy-4-hexyl-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-methyl-4-iodo-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2-methyl-4-fluoro-α-chloroacetanilide,N-(1,3-dioxolan-5-ylmethyl)-2,6-diethyl-α-chloropropionanilide,N-(1,3-dioxolan-5-ylmethyl)-N-α-chlorobutanoyl-2,6-diethylaniline,N-(1,3-dioxolan-5-ylmethyl)-N-α-bromopentanoyl-2,6-diethylaniline,N-(1,3-dioxolan-5-ylmethyl)-N-α-chlorohexanoyl-2,6-diethylaniline,N-(1,3-dioxolan-5-ylmethyl)-N-α-chloroheptanoyl-2,6-diethylaniline,N-(1,3-dioxolan-5-ylmethyl)-N-α -chlorooctanoyl-2,6-diethylaniline andthe like.

For practical use as herbicides the compounds of this invention aregenerally incorporated into herbicidal compositions which comprise aninert carrier and a herbicidally toxic amount of such a compound. Suchherbicidal compositions, which can also be called formulations, enablethe active compound to be applied conveniently to the site of the weedinfestation in any desired quantity. These compositions can be solidssuch as dusts, granules, or wettable powders; or they can be liquidssuch as solutions, aerosols, or emulsifiable concentrates.

For example, dusts can be prepared by grinding and blending the activecompound with a solid inert carrier such as the talcs, clays, silicas,pyrophyllite, and the like. Granular formulations can be prepared byimpregnating the compound, usually dissolved in a suitable solvent, ontoand into granulated carriers such as the attapulgites or thevermiculites, usually of a particle size range of from about 0.3 to 1.5mm. Wettable powders, which can be dispersed in water or oil to anydesired concentration of the active compound, can be prepared byincorporating wetting agents into concentrated dust compositions.

In some cases the active compounds are sufficiently soluble in commonorganic solvents such as kerosene or xylene so that they can be useddirectly as solutions in these solvents. Frequently, solutions ofherbicides can be dispersed under super-atmospheric pressure asaerosols. However, preferred liquid herbicidal compositions areemulsifiable concentrates, which comprise an active compound accordingto this invention and as the inert carrier, a solvent and an emulsifier.Such emulsifiable concentrates can be extended with water and/or oil toany desired concentration of active compound for application as spraysto the site of the weed infestation. The emulsifiers most commonly usedin these concentrates are nonionic or mixtures of nonionic with anionicsurface-active agents. With the use of some emulsifier systems aninverted emulsion (water in oil) can be prepared for direct applicationto weed infestations.

A typical herbicidal composition according to this invention isillustrated by the following example, in which the quantities are inparts by weight.

EXAMPLE 18

    Preparation of a Dust                                                         Product of Example 3      10                                                  Powdered Talc             90                                              

The above ingredients are mixed in a mechanical grinder-blender and areground until a homogeneous, free-flowing dust of the desired particlesize is obtained. This dust is suitable for direct application to thesite of the weed infestation.

The compounds of this invention can be applied as herbicides in anymanner recognized by the art. One method for the control of weedscomprises contacting the locus of said weeds with a herbicidalcomposition comprising an inert carrier and as an essential activeingredient, in a quantity whch is herbicidally toxic to said weeds, acompound of the present invention. The concentration of the newcompounds of this invention in the herbicidal compositions will varygreatly with the type of formulation and the purpose for which it isdesigned, but generally the herbicidal compositions will comprise fromabout 0.05 to about 95 percent by weight of the active compounds of thisinvention. In a preferred embodiment of this invention, the herbicidalcompositions will comprise from about 5 to about 75 percent by weight ofthe active compound. The compositions can also comprise such additionalsubstances as other pesticides, such as insecticides, nematocides,fungicides, and the like; stabilizers, spreaders, deactivators,adhesives, stickers, fertilizers, activators, synergists, and the like.

The compounds of the present invention are also useful when combinedwith other herbicides and/or defoliants, dessicants, growth inhibitors,and the like in the herbicidal compositions heretofore described. Theseother materials can comprise from about 5 percent to about 95 percent ofthe active ingredients in the herbicidal compositions. Use ofcombinations of these other herbicides and/or defoliants, dessicants,etc. with the compounds of the present invention provide herbicidalcompositions which are more effective in controlling weeds and oftenprovide results unattainable with separate compositions of theindividual herbicides. The other herbicides, defoliants, dessicants andplant growth inhibitors, with which the compounds of this invention canbe used in the herbicidal compositions to control weeds, can includechlorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DB),2,4-DEB, 4-CPB, 4-CPA, 4-CPP, 2,4,5-TB, 2,4,5-TES, 3,4-DA, silvex andthe like; carbamate herbicides such as IPC, CIPC, swep, barban, BCPC,CEPC, CPPC, and the like; thiocarbamate and dithiocarbamate herbicidessuch as CDEC, metham sodium, EPTC, diallate, PEBC, perbulate, vernolateand the like; substituted urea herbicides such as norea, siduron,dichloral urea, chloroxuron, cycluron, fenuron, monuron, monuron TCA,diuron, linuron, monolinuron, neburon, buturon, trimeturon and the like;symmetrical triazine herbicides such as simazine, chlorazine, atraone,desmetryne, norazine, ipazine, prometryn, atazine, trietazine, simetone,prometone, propazine, ametryne and the like; chloroacetamide herbicidessuch as 4-(chloroacetyl)morpholine, 1-(chloroacetyl)piperidine and thelike; chlorinated aliphatic acid herbicides such as TCA, dalapon,2,3-dichloropropionic acid, 2,2,3-TPA and the like; chlorinated benzoicacid and phenylacetic acid herbicides such as 2,3,6-TBA, 2,3,5,6-TBA,dicamba, tricamba, amiben, fenac, PBA,2-methoxy-3,6-dichlorophenylacetic acid,3-methoxy-2,6-dichlorophenylacetic acid,2-methoxy-3,5,6-trichlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoicacid and the like; and such compounds as aminotriazole, maleichydrazide, phenyl mercuric acetate, endothal, biuret, technicalchlordane, dimethyl 2,3,5,6-tetrachloroterephthalate, diquat, erbon,DNC, DNBP, dichlobenil, DPA, diphenamid, dipropalin, trifluralin, solan,dicryl, merphos, DMPA, DSMA, MSMA, potassium azide, acrolein, benefin,bensulide, AMS, bromacil,2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione,bromoxynil, cacodylic acid, CMA, CPMF, cypromid, DCB, DCPA, dichlone,diphenatril, DMTT, DNAP, EBEP, EXD, HCA, ioxynil, IPX, isocil, potassiumcyanate, MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OCH, paraquat, PCP,picloram, DPA, PCA, pyrichlor, sesone, terbacil, terbutol, TCBA,brominil, CP-50144, H-176-1, H-732, M-2901, planavin, sodiumtetraborate, calcium cyanamid, DEF, ethyl xanthogen disulfide, sindone,sindone B, propanil and the like.

Such herbicides can also be used in the methods and compositions of thisinvention in the form of their salts, esters, amides, and otherderivatives whenever applicable to the particular parent compounds.

Weeds are undesirable plants growing where they are not wanted, havingno economic value, and interfering with the production of cultivatedcrops, with the growing of ornamental plants, or with the welfare oflivestock. Many types of weeds are known, including annuals such aspigweed, lambsquarters, foxtail, crabgrass, wild mustard, fieldpennycress, ryegrass, goose grass, chickweed, wild oats, velvetleaf,purslane, barnyardgrass, smartweed, knotweed, cocklebur, wild buckwheat,kochia, medic, corn cockle, ragweed, sowthistle, coffeeweed, croton,cuphea, dodder, fumitory, groundsel, hemp nettle, knawel, spurge,spurry, emex, jungle rice, pondweed, dog fennel, carpetweed,morningglory, bedstraw, ducksalad, naiad, cheatgrass, fall panicum,jimsonweed, witchgrass, switchgrass, watergrass, teaweed, wild turnipand sprangletop; biennials such as wild carrot, matricaria, wild barley,campion, chamomile, burdock, mullein, roundleaved mallow, bull thistle,hounds-tongue, moth mullein and purple star thistle; or perennials suchas white cockle, perennial ryegrass, quackgrass, Johnson grass, Canadathistle, hedge bindweed, Bermuda grass, sheep sorrel, curly dock,nutgrass, field chickweed, dandelion, campanula, field bindweed, Russianknapweed, mesquite, toadflax, yarrow, aster, gromwell, horsetail,ironweed, sesbania, bulrush, cattail, wintercress, horsenettle,nutsedge, milkweed and sicklepod.

Similarly, such weeds can be classified as broadleaf or grassy weeds. Itis economically desirable to control the growth of such weeds withoutdamaging beneficial plants or livestock.

The new compounds of this invention are particularly valuable for weedcontrol because they are toxic to many species and groups of weeds whilethey are relatively nontoxic to many beneficial plants. The exact amountof compound required will depend on a variety of factors, including thehardiness of the particular weed species, weather, type of soil, methodof application, the kind of beneficial plants in the same area, and thelike. Thus, while the application of up to only about one or two ouncesof active compound per acre may be sufficient for good control of alight infestation of weeds growing under adverse conditions, theapplication of ten pounds or more of an active compound per acre may berequired for good control of a dense infestation of hardy perennialweeds growing under favorable conditions.

The herbicidal toxicity of the new compounds of this invention can beillustrated by many of the established testing techniques known to theart, such as pre- and post-emergence testing.

The herbicidal activity of the compounds of this invention wasdemonstrated by an experiment carried out for the pre-emergence controlof a variety of weeds. In this experiment small plastic greenhouse potsfilled with dry soil were seeded with the various weed seeds.Twenty-four hours or less after seeding the pots were sprayed with wateruntil the soil was wet and the test compound formulated as an aqueousemulsion of an acetone solution containing emulsifiers was sprayed atthe indicated concentration on the surface of the soil.

After spraying, the soil containers were placed in the greenhouse andprovided with supplementary heat as required and daily or more frequentwatering. The plants were maintained under these conditions for a periodof from 15 to 21 days, at which time the condition of the plants and thedegree of injury to the plants was rated on a scale of from 0 to 10, asfollows: 0 = no injury, 1,2 = slight injury, 3,4 = moderate injury, 5,6= moderately severe injury, 7,8,9 = severe injury and 10 = death. Theeffectiveness of this compound is demonstrated by the following data:

                  TABLE I                                                         ______________________________________                                                         Injury Rating                                                                 Product of Example 3                                                          Concentration (lbs/acre)                                     Weed Species     10                                                           ______________________________________                                        Yellow Nutsedge  10                                                           Wild Oats        7                                                            Jimsonweed       6                                                            Velvetleaf       1                                                            Johnson Grass    7                                                            Pigweed          10                                                           Mustard          5                                                            Yellow Foxtail   10                                                           Barnyardgrass    10                                                           Crabgrass        10                                                           Cheatgrass       10                                                           Morningglory 4                                                                ______________________________________                                    

The herbicidal activity of the compounds of this invention was alsodemonstrated by an experiment carried out for the post-emergence controlof a variety of weeds. In this experiment the compound to be tested wasformulated as an aqueous emulsion and sprayed at the indicated dosage onthe foliage of the weeds that have attained a prescribed size. Afterspraying the plants were placed in a greenhouse and watered daily ormore frequently. Water was not applied to the foliage of the treatedplants. The severity of the injury was determined 10 to 15 days aftertreatment and was rated on the scale of from 0 to 10 heretoforedescribed. The effectiveness of this compound is demonstrated by thefollowing data:

                  TABLE II                                                        ______________________________________                                                         Injury Rating                                                                 Product of Example 3                                                          Concentration (lbs/acre)                                     Weed Species     10                                                           ______________________________________                                        Yellow Nutsedge  9                                                            Wild Oats        7                                                            Jimsonweed       5                                                            Johnson Grass    8                                                            Pigweed          10                                                           Mustard          10                                                           Yellow Foxtail   8                                                            Barnyardgrass    9                                                            Crabgrass        7                                                            Morningglory     3                                                            Bindweed         5                                                            ______________________________________                                    

We claim:
 1. A compound of the formula ##SPC5##wherein Y is selectedfrom the group consisting of hydrogen, lower alkyl and halogen; R¹ isselected from the group consisting of hydrogen, lower alkyl and loweralkoxy; R² is lower alkyl; R³ and R⁴ are independently selected from thegroup consisting of hydrogen and lower alkyl; X is halogen; and n is theinteger 1 to
 2. 2. The compound of claim 1,N-(1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-α-chloroacetanilide.
 3. Thecompound of claim 1,N-(1,3-dioxolan-5-ylethyl)-2,6-diethyl-α-chloroacetanilide.
 4. Thecompound of claim 1,N-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-methoxy-α-chloroacetanilide. 5.The compound of claim 1,N-(1,3-dioxolan-5-ylmethyl)-2-ethyl-4-chloro-α-chloroacetanilide.
 6. Thecompound of claim 1,N-(1,3-dioxolan-5-ylmethyl)-2,4,6-trimethyl-α-chloroacetanilide.
 7. Thecompound of claim 1,N-(1,3-dioxolan-5-ylmethyl)-2,6-dimethyl-4-bromo-α-chloroacetanilide 8.The compound of claim 1,N-(2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-α-bromoacetanilide.